Holding On
by lindygirl0408
Summary: How will a mother's decision influence her daughter's life and relationships? Will Rory have the life her mother expected for her? Only time will tell...
1. Prologue

_**Author's Note: **_**_So, here it is! The full prologue to "Holding On."_**

**_This will be an AU fic. I hope you like this little taste!_**

_**Disclaimer:** I do not claim to own the rights to "Gilmore Girls" or it's characters. No copyright infringement intended._

Holding On: Prologue

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Why is it that every dramatic part of someone's life story contained a torrential downpour? Tonight was no different for the young girl standing under the awning that she had been under a thousand times before.

She had lost track of how long she had been standing there, staring at what was most certainly going to bring her to her demise. The last minute she calculated was twelve. Twelve minutes standing in one spot in the middle of the night, fumbling for the courage she needed to do what was right.

It had been just over a year since the last time she had passed under the awning that was now her only shelter from the monsoon, except she had been leaving- running to put it more accurately. That fateful night, she didn't even look back or think twice about her decision. (Coincidentally, it had been raining that day as well.) She was suffocating and she needed to get out. Running was the only way to break away from the future she was being forced into. It was a future she knew was wrong.

So here she stood, just fifteen months later, with so many things unsaid, trying to compel her body to move and having an internal battle with her thoughts.

_Just one arm…a leg? Blink? Something, move _something_! _She finally took a careful step forward and raised her arm, pausing again, and lowered her arm back down. _It's just an inanimate object… Everything's going to be fine. _She had moved on from feeling complete terror and was now trying denial. _How much worse could it be? What's done is done, and…a year is long enough, right?_

The confusion she felt was too much to handle and she started to lose the battle within her. Tears started to fall down her cheeks, mimicking the rain behind her. She turned on her feet ready to dart away once more when the bundle she was carrying finally stirred and let out a whine. Just a single sound from the daughter she loved more than anything else was enough to put her on the right path again. Walking back toward the object of her focus from before she closed her eyes and hesitantly pressed the glowing button in front of her (it's just an inanimate object), and let out the breath she had been holding.

The sound of the chimes from the doorbell sent chills down her spine. She had to do this, not for herself, but for the daughter that was her world. Her tears were still free flowing from her puffy, sorrow colored, blue eyes. The sound of grumbling and footsteps caused her to take in a sharp breath, as more tears fell. She wasn't sure if it was the pain of the last year or the fear she now had that was causing the water to drain from her eyes, but she couldn't stop it. She looked behind her, then back down to the sleeping girl in her arm. _This is for you baby. No turning back now._

The footsteps stopped at the door and the sound of clicking locks drowned out the storm behind her. The door swung open with hesitation and she was met with eyes full of anger, sadness, and confusion. Taking in a ragged breath, she finally spoke through her broken, grief-strained voice, "M…Mom?"

Without words, the woman opened the door further, still gaping at her young daughter, silently inviting her inside. The two stood in one place, neither breaking eye contact until the younger Gilmore began to speak, "Mom…" The words were more difficult to puzzle together than she had anticipated. Another silence dragged on while she tried to piece a sentence together. With a cleansing sigh, she gave another attempt, "Mom, I-"

"It's late Lorelai, what are you doing here?" Emily Gilmore was well practiced at the art of indifference. She had her daughter to thank for that gift. The list of disappointments with Lorelai's name on top was sizable. The most recent blow, she was still recovering from. Waking up to find a note which informed her that her seventeen-year-old daughter had run away with her infant child threw even the great Emily off kilter.

Lorelai gazed toward her mother, stunned. She was left without her wit. A first for Lorelai Gilmore, from her recollection. Even when she had to tell her mother of her _forbidden p_regnancy she managed to make a few "Hester Prinn" jokes. She had even gone so far as to cut out a scarlett-colored letter "P" (for pregnant) from an old pair of sweats, offering to wear it so that Emily wouldn't have to endure the task of telling everyone they knew. Naturally, that plan didn't go over well, but even at what she thought was her lowest point, she had seen concern and love reflected in her mother's eyes. Tonight all she saw reflected in those eyes was a little sleep deprivation. She needed to find a way to break the ice, and why not dive in head first? _Okay, maybe feet first_, she thought. "Th-The place looks beautiful...mom. Really, I never knew that changing the stain on the floors could make such a difference. It's great. Really, really great." She carefully shifted the weight in her arms to tuck her damp hair behind her ear.

"Is that all Lorelai? It is twelve-thirty at night. This is highly inappropriate. If you've got nothing of importance to say, then I ask that you please leave so I might return to sleep."

"No, that isn't what I came her to say, I-" she was interrupted by the sob that escaped her chest. Through staggering breaths and muffled words she continued, "I left because I thought I knew what was best. You were trying to force me into a life that I'm in no way near ready for. I can't marry Christopher mom, we both need to figure out who we are alone before we try to make a life together." She paused trying to gauge her mother's reaction. She took the silence as permission to carry on, "I wasn't trying to punish you or dad. I just couldn't continue on the way things were going. I was Alice falling down the hole, except that there was no bottom to the madness." She let out a long breath. "I guess I just want you to know that I finally understand that what you were doing, although drastically old-fashioned, was still out of concern and love. Yes, all of Hartford will forever look at me as 'The Girl Who Got Knocked-up At Sixteen' but I don't want them to see us as a broken family. I'm sorry. I'm so sorry for everything. I don't want my daughter to miss out on the most influential people in her life, and that especially includes her grandparents. I will not agree to marry Chris, but I want us to move forward. I want to feel like a family. If not for us, then for this innocent girl. She's so beautiful mom. I don't want you to miss anything in her life. Dad too. I want...I want to come-"

The deep voice from the stairs finished her sentence for her, "You want to come home." Richard walked towards the three most important women in his life, kissed Emily gently on her forehead and pulled Lorelai into his warm embrace while caressing the satin-smooth cheek of the sleeping child. "Come on Emily, let's get our girls to bed." And with those words, the Gilmore's walked up the stairs as a family. None sure of what Lorelai's return would change in Rory's life.

"Wait!" Lorelai whispered across the corridor to her parents. She ran into the room, _her_ room, laid Rory carefully in the crib that remained from her last night here, and jogged back to the hallway, pulling two pieces of paper from a folder in her bag. She handed them to her father and waited, holding her breath for their reaction.

Richard's face took on a new color; he looked...warm, and passed the first paper to Emily while her face did the same and his eyes bugged out of his head from the second paper. "How?" was all he could speak.

"I doubled up my work load, took night classes, and had a lot of help. I didn't want to come back here until I knew I could make you proud...somehow. I finished high school and made out dozens of applications for college, determined to come back with something," a small smile of accomplishment appeared on her face.

Richard handed the second paper to Emily and pulled his daughter in for another hug. "Yale! Lorelai, is this a joke? Because if it is, I assure you, it isn't funny."

"No mom, this is real. I am going to business school at Yale, and someday, I'm going to own my own inn. I have to do this...I _need_ to do this. For me, and for Rory. And I can't do it without either of you. Well, if you want to help..." she trailed off.

"I'll write the check for tuition tomorrow," Richard beamed, kissed his daughter's head and strolled back to bed with a silent Emily following behind.

Lorelai turned to head back to her room and laughed softly, "Who knew all it would take to make Emily Gilmore speechless was to do something right?" She continued to smile as she peered at the sleeping form of her daughter. She silently promised herself there that Rory would not have the same feelings she'd had while growing up in this house. Rory would always have choice where she didn't. She went over to her desk, and pulled out a piece of blank white paper and a dark red marker, still smiling to herself.

She carefully admired her artwork that she had securely hung over her daughter's crib and gave a chuckle. _Maybe I would have gone to Harvard given the choice. _She considered that for a moment still looking at the elegant letter "H" she had colored, and laughed again. _That would have been a sure-fire way to torment Richard and Emily. It would have been so simple! But that doesn't matter anymore. The Gilmore legacy is still intact for now, and Rory will always have a choice. I'll make sure of it. _And with those last thoughts, she lay on her bed and quickly went to sleep.

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**_Author's Note: So what did you think? Worth continuing?_**

**_(If yes, there will be a small time jump so that the story will become more focused on Rory)_**

**_Please Review! Thanks!_**


	2. Poison and Promise

_**The long awaited first chapter of Holding On! Sorry for the wait, I hope it's worth it! Thank you all for your great reviews! It means so much to me, and I would love your continued imput! I hope I was able to incorporate some of your great ideas, and if I haven't, there will be plenty of time :)**_

_**Disclaimer:** I do not claim to own the rights to "Gilmore Girls" or it's characters. No copyright infringement intended._

Chapter 1: Poison and Promise

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"Mom, I am so tired of these Friday night dinners! When do I get to be a 'normal' teenager?" Rory called from her room. "No remarks about me being 'normal' please. I'm not in the mood." After nearly fifteen years of the same Friday night plans, a teenager is bound to get a little bored; especially when the dinner was with her grandparents. It was a well-known fact that the Hayden's weren't the biggest fans of Lorelai and her choice to keep "the child," but over time Straub and Francine Hayden developed a small soft spot for their only grandchild. Friday night dinners at the main house were part of the agreement made with Richard and Emily when they allowed Lorelai to move into their pool house to give her a chance to live a bit more on her own while attending Yale. The other part of the agreement was that Lorelai had to invite the Hayden's to attend these weekly dinners so they, too, could be part of Rory's life if they so choose. So here they were, unable to make any real plans on a Friday night because of, yet another, family obligation.

"I know kid, I know. Just think, in just over a year you'll be off to Harvard and free from the weekly obligation, where as I will be stuck in this cycle, maybe forever! Forever's a really long time you know! I don't think there is another mother in the world that would give up her every Friday night in order to insure her daughter's future. "

"Wow, pulling out the 'Sacrificing Mother' card and it's not even six o'clock yet. You've been into the Halloween candy again haven't you? You always get defensive after you've had too much sugar. We are not buying the leftover holiday candy next time. I don't care how cheap it is after the actual holiday. For the sake of our relationship, it is banned from this house. Is it even safe to eat six-month-old candy? I'm guessing not." Rory continued to dress for the evening, eager for the dinner to be over so she could spend the night planning out her extra-curriculars for the next school year and perusing Harvard's new course catalog. "And mom? You are going to be out of here so fast, I know it! The Inn is almost done and there's no doubt in my mind that it will be a great success. Stars Hollow is a great tourist town, and it's perfect for your Inn now that the Independence Inn has been sold to a major chain. They'll turn it into a horrifying Bed & Breakfast in no time. I am so proud of you."

After another 45 minutes of primping, the two Lorelai's made their venture across the yard to the Gilmore mansion and to another night of forced-polite conversation. The biggest news through dinner was that Christopher was still nowhere to be found. He would occasionally send a post card to Rory just so she knew he was okay, but after his last attempt to marry Lorelai two years ago, he took to the road. His timing was never very good when it came to his relationship with Lorelai. She had finally started moving with plans to open an inn when Chris showed up, out of the blue, from his most recent venture in California (another failed venture) and practically begged her and Rory to come across the country with him while he searched for another life for himself. Lorelai hated that he always seemed to come to her and Rory when he had nothing else left. She loved Christopher, but he just wasn't in a place where they could be a family.

The best news was that Straub and Francine were taking a holiday and would be absent from the next two dinners. Rory and Lorelai's glee, however, was halted at the information that next Friday they were expected to attend a reunion party for Yale alumni, seeing as Lorelai was also included in the alumni category.

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The following Monday arrived quickly, too quickly in Rory's opinion as her phone buzzed loudly on her nightstand. "I am assuming you're dying because that would be they only reason for anyone to call me at five in the morning."

Rory could practically hear the eye roll coming from the other end of the phone call. "Do you want to hear the news or not?"

"Okay Paris, what is so important that you had to wake me up an hour before my alarm went off?"

"Madeline just called me to tell me that she heard from Louise that we're getting three new students today, seniors! Can you believe it? Chilton almost never takes students this late in the school year, let alone three, and in their last two months of school, no less. This is absurd! They must be really high on the money ladder or something…"

"Relax Paris. I don't know why that was important enough to wake me. Go back to sleep or something, and you'd better have a hot coffee in hand when I get to school to make up for the sleep deprivation you've caused me. "

"Don't you get it Gilmore? These new students could be our connections into the Ivy League world. Just think of the possibilities! I need to brainstorm, gather up all the-"

"Good bye Paris," Rory ended the call, rolled over, and tried to get back to her last 52 minutes of sleep. Unfortunately, some of what Paris had said got her mind turning and Rory couldn't help but wonder if these new students might be her ticket into Harvard; if they had parents that had attended, or if they had any pull with admissions officers. The sound of her alarm pulled her out of her thoughts and Rory proceeded to get ready for the day.

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All of Chilton was abuzz about the new students that had arrived at their school. Rumors were flying about the three boys and their most recent acts of mischief and pranking that had gotten them kicked out of, yet another, boarding school. Rumors included the fact that they had all been to at least five different boarding schools each, one of the students sleeping with the dean's wife, parking the dean's car at the bottom of a lake, and, Rory's favorite, one of the students posing naked in compromised positions with all of the statues around campus while the others photographed the act. While it was obvious that the newcomers wouldn't be any help at getting her a shot at Harvard, she couldn't help but wonder how they were able to get into Chilton after all that they had done. It would take some serious money to turn Headmaster Charleston's head, of that she was certain.

Rory had made it all the way to lunch before spotting one of them. Louise was describing each of the boys to her and Paris when one of them walked past their table, turned around with a thoughtful expression, and headed back toward them. He was average height with medium-brown hair, and he looked stressed out. "Look, I'm not supposed to say anything, but I would feel guilty if I didn't warn four unsuspecting, beautiful women that something is wrong with your food…" The four girls looked at each other and back at the loafer-clad boy at the head of their table with confusion. "Don't eat the potatoes," the guy said with a wink and started to walk off.

"And who do we thank for this information?" Louise purred before he could take two steps.

He glanced over her and smiled approvingly, "I'm Colin. Colin McCrae, and believe me when I say that I am the most trustworthy of my friends and myself. They don't want to be in classes today, hence the potato warning. If this works, I expect to see the four of you out in the parking lot where you can proceed to thank me. Bye ladies."

Just as Colin made his way out the door, Rory began to notice other students looking uncomfortable and then quickly making their way to the nearest exit, one by one. Eventually the entire cafeteria was in a panic and all the students were heading for the bathroom within closest proximity. Chilton was forced to send everyone home because of the widespread outbreak of…'digestion issues' among students and faculty. It was exactly what those troublemakers had in mind, and the four girls knew it. They definitely had to be grateful for Colin's chivalry, but Rory couldn't get the feeling that maybe their 'rescue' was also part of the plan.

Once Rory had her bag packed she walked to Paris' locker where they were waiting for Madeline and Louise. "So interesting day, huh?"

"Don't look so smug Gilmore. Obviously I was wrong about the…quality of student that could get into Chilton, but at least we know that they aren't above bribing and name dropping to get somewhere in life. That McCrae kid? He's the son of Andrew McCrae. Big-shot Lawyer, won a billion dollar suit last year against some pharmaceutical company? Ring any bells?"

"Wow, yeah. I think my grandpa does some sort of insurance business with an Andrew McCrae, and I'm sure grandma knows them too. His mother is probably part of some organization or committee with her."

"Oh I highly doubt that. The only other divorce that was more publicized than my parent's last year was the fourth divorce of Andrew McCrae. He goes through wives like old newspapers, and they stay the same age as he gets older. It's disgusting. No wonder his son is so troubled."

Paris continued her rant until the other two girls showed up, and together, they made their way to the parking lot discussing the day's events. It wasn't hard to spot Colin. He was standing by a shiny Mercedes at the front of the lot looking arrogant. "Well, it seems that a few of us are immune to this strange bug that has infected this fine establishment. How lucky for us," Colin beamed.

"You guys are out of your minds! But incredibly talented at what you do," Madeline complemented and held out her hand. "I'm Madeline Lynn, and I guess I owe you a thank you for saving me from the horrors that went on in school today." She smiled and gave him a light kiss on the cheek.

"It was my pleasure to be of service to you Madeline Lynn," Colin replied with a half-smile.

"Louise Grant, and I would be happy to return the favor to you any time you need something," she informed Colin in a whisper as she went in for a kiss on his other cheek.

Before she made contact, though, she was interrupted by another of the new students, "Oy! If you're passing out kisses I think it only fair to include the rest of us Luv," the tall dark-haired guy announced in a thick Austrailian accent, made his way next to Colin, and put his arm across his shoulder. "Afterall, if it wasn't for me and my mate over there, " he pointed to the blonde making his way over, "we'd all be sittin' in class wishin' we were elsewhere. So, what have we missed?"

"Don't worry Finn; I wouldn't have taken all the credit here. You only missed two introductions. This is Madeline," he gestured toward her first then to Louise, "and this is Louise. As you can see, they were tipped off by a very kind soul about the 'potato problem'."

"Yeah, always a blabbermouth when there's a pretty face involved, or four in this case. You're pathetic mate. And who is this beauty standing before me?" Finn reached out for Paris' hand, but she moved before he could grab it.

"I have no patience for audacious pranks and immature boys. I only came here to thank you for warning us, but don't expect me to grovel at your feet." Paris stormed off just as the third guy joined the group.

"Wow, she looked angry. She didn't eat any potatoes today did she? I heard there was something wrong with them," the blonde looked to the three remaining girls with a knowing smirk displayed across his face.

"No, that's just Paris. She's always looking to be angry at someone," Louise chimed in.

"I will have to remember that then, for next time. So who do we have here?" He gestured toward the three girls, while looking them over and stopping on Rory who looked a little steamed.

"Let me see if I remember who's who," Finn chimed in. He reached for Louise's hand and brought it to his lips, "Lovely Louise," he then did the same to Madeline, "and Marvelous Madeline, right?"

While Madeline and Louise giggles with flirtation, the rage that had been festering in Rory finally came out all at once, "Okay, you cross the line with cheesy nicknames. Do any of you three realize that some of us actually want to go to college? Some of us want to do well in school?" The arrogance of these boys was enough to infuriate anyone, but Gilmore's have no patience for arrogance. She started wagging her finger and pointing between the boys while the blonde continued to stare. "We're not impressed by your care-free 'I don't need school' attitudes. We worked for our place here; our daddies didn't buy us our places. I just lost half of an entire day because you three can't be responsible for once. I want to go to a good college and I am going to earn it. Something you have obviously never strived for in your entire lives!"

As Rory finally took a breath, Colin interjected, "I'm sorry, can I at least know who I'm being insulted by? I mean, if we're to continue standing here, I would at least like to know who it's for."

Rory scowled and was about to speak, but someone else did for her, "Rory Gilmore…I'd know that finger wag anywhere."

"I know I will regret asking this, but how exactly is it that you know who I am?" Rory questioned suspiciously.

"Wow, the scowl is even the same. It's really uncanny…" the blonde went on.

"Okay, and?"

"The last time I saw you we were in a very similar predicament except I had just tossed your copy of The Odyssey out the third story window of the library in my house. You weren't paying attention to me, so naturally, I took action. I had no choice," he gave her a devious smile, knowing that the memory would add to her anger.

"Ugh, Logan Huntzberger. I always knew I'd have to encounter you again someday. And just as I expected, it isn't a great reunion. It appears that you haven't changed at all, mentally, since you were ten. How charming. Well, if you'll excuse me…"

"Okay, Rory, wait! I'm sorry. It was just a stupid prank. Everyone will be fine in a couple of hours and we just wanted one afternoon of freedom before we had to start buckling down for finals, alright? It won't happen again. I promise. Come on, you aren't even a little relieved to have some time off? You can't seriously still be angry about something I did seven years ago?" He paused and remembered something, "Hey, I heard that the Ivy Leagues just put out new course catalogs. I'm sure there are some exciting things to look at in there." He stopped as he saw one side of her mouth twitch in a smile briefly. She was obviously still as much of a book worm as he remembered. "The guys and I will even take you girls out for coffee to make up for the inconvenience, right boys?"

Both boys answered with a, "yeah," and a, "definitely," and looked back at Rory for approval.

Of course they had her at the mention of her favorite hot beverage, but Rory pretended to contemplate for a few moments while Logan and his friends looked at her expectantly. "I will agree on one condition."

"Name it," Finn agreed.

Rory looked at her friends with a devilish grin, "We want to see the pictures that had one of you kicked out of your last school." She smiled with satisfaction knowing that all the rumors had to be true (and most likely spread by these three menaces to guarantee their reputations as rebel-rousers.) Who would have thought that this one event would be the beginning of life-long friendships?

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_**Okay, it's 4am, so please tell me if something doesn't make sense! Or maybe if you enjoyed reading! =) I have written ahead in this story so the next update shouldn't be quite so distant! Thanks for stopping by!**_


	3. Night in Shining Armani?

_**I feel like this is becoming a pattern. Here it is, 4am and I decided to edit and post the next chapter. I hope it you enjoy this (American) Thanksgiving treat! Happy Thanksgiving to anyone celebrating today!**_

_**Disclaimer:**__ I do not claim to own the rights to "Gilmore Girls" or it's characters. No copyright infringement intended._

2. Knight in Shining Armani?

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Coffee turned into dinner which turned into after-dinner coffee followed by a movie at Colin's house (his dad was away on business as per usual.) The boys revealed their adventures in boarding school, the girls went over the way things worked at Chilton, and the night flew by. For the rest of the week the group ate together at lunch, including Paris who found another target to direct her rath: Brad Langford had also transferred back to Chilton.

In what seemed like a blink of an eye, Friday night had arrived and, once again, Rory and Lorelai were rushing to get ready for dinner at the main house and, once again, they were running a bit behind.

"How much time?" Lorelai shouted from her bedroom while attempting to hop to the bathroom and put her second shoe on at the same time.

"Eight minutes!" Rory called back, while brushing her teeth and pulling her tights on. She spit her toothpaste in the kitchen sink, grabbed her purse (containing her current book of the day), and raced to put her shoes on. She checked the clock, _Five minutes to spare_. "Do you think she'd even notice if we were late?"

Before Lorelai could respond a shrill, deafening sound dropped her to the ground. "You two had better be over here in less than five minutes or I will have the pool house fumigated and you'll have to move back in here. I mean it Lorelai, don't push me." The worst part of living in Emily's pool house was the intercom connected to the main house which only had one volume: ear-bleeding loud.

Rory ran to the nearest intercom to respond, "We're walking out the door right now Grandma. See you in a few minutes." She ran toward her mother's room, "Mom, let's go! Are you almost- Mom! Your dress isn't even zipped up! Grab your stuff and come on! Put your shoes on while we're walking, because there is no way I want to move into that house for a week or two!"

"Right! Moving, I'm moving…got the bag…got the shoes…and gone! You can zip me up on the way!" Lorelai grabbed her things and both headed for the door.

**X**X**X**X**X**X**X**X*

"I find it a little excessive that we have to ring the doorbell before going in. It's not like we're strangers, or fly-by-night salesman," Lorelai complained as they reached the main entry.

"We expect them to knock before coming into the pool house, and they own it!" Rory retorted. "I find it excessive that I had to come to this party even though they both know I'm going to Harvard. Grandpa is probably going to have his buddies help him to relive 'The Glory Days' in hopes that I will reconsider, again." It was well known that Richard and Emily didn't want Rory to attend any school other than Yale. Lorelai wouldn't mind her attending, it was her Alma Mater after all, but she made sure to keep the promise she made to her baby girl so many years ago. She would always have her choice.

"I'm sure your right about that. It's probably the only reason they're throwing the party. We'll slip out before they start drinking too much brandy; that way they won't have started the singing yet. Sorry kid, being a Gilmore sometimes comes with a little crazy." Lorelai pushed the button and they were welcomed into the house.

Emily was first to reach the door. As she opened it, she glanced at her sparkling watch, "Well, thirty seconds to spare. If I didn't know better, I'd say you weren't very thrilled to be here. Well. Don't just stand in the door way, come in. I've started serving the appetizers and dinner will be served within the hour. Don't forget to greet your father. He is in a particularly good mood tonight." She was about to continue her direction when a server walked by with a tray of salmon puffs. "Is that _garnish? _Young man? Young man!" And with that, Emily was gone, chasing after the poor soul who didn't follow her orders.

Half an hour had past and Rory found herself cornered by the only two people her age at the party, both boys, and both shamelessly trying to pick her up. She politely nodded and agreed wherever necessary with no interest in the conversation and no visible escape from her new fate. She was about to use the 'I'm going to powder my nose' excuse when an arm slid around her shoulder.

"Darling I'm sorry I'm late. Traffic was a nightmare. Are you mad? Please don't be mad." Rory looked, in shock, up to the man at her side and gave him a disgruntled look. "You're mad. Don't look at me that way, it will never happen again. Were you having a good conversation before I interrupted?" He gave her a quick wink as a sign to play along.

"Um, no _darling_, you didn't interrupt," she started, noticing the looks on the other guy's faces. They clearly thought otherwise. She wrapped her arm around his waist for added emphasis. She was going to have a little fun with this. "Well, don't be shy _sweetums_, introduce yourself." Yep, just as expected, the two across from her winced at the sickly sweet term of endearment.

"My apologies gents, I'm Derek, Rory's boyfriend." Rory looked satisfied that she was able to get the stranger in Armani to reveal his name; at least she had a name to go with the face.

The boys looked at each other, and then back at Derek when one spoke, "You're her boyfriend? She never mentioned a boyfriend."

"Yeah, going on a year and a half. She can be a bit vengeful and was probably trying to make me jealous seeing as I'm nearly forty five minutes late." He glanced over at Rory and looked apologetic, "I'm so sorry _precious_, you win okay? It nearly killed me to see you talking to them. You want me to announce it to the room? I will. I'm jealous! I want the world to know!" As he started to raise his voice and gain the attention of some nearby guests, Rory turned to him with utter embarrassment written all over her face. She quickly put her hand over his mouth and pleaded with her eyes for him to take it down a notch. He nodded and spoke again, "Can we please be in love again and go?"

Rory looked at her previous companions with mock apology, "I'm so sorry guys. It looks like we've made up. It was nice meeting both of you, and good luck at Yale next year." She turned to look at Derek, "Let's go _cuddle-bear_." They both turned and headed outside, Derek leading her by the hand. "Not that I don't trust you or anything, but where are we going?"

Derek chuckled and pointed toward the pool house, "To the party of course!" Rory looked confused but continued to follow. She was just happy to be away from the other two guys. "Okay wait, "Derek stopped abruptly. "Did you seriously call me 'cuddle-bear?' Talk about emasculating. It's a good thing we aren't actually dating because there's no way I'd ever be aroused after hearing that." He laughed again and resumed his pulling of Rory toward the pool house.

"Sorry to make you question your manhood," Rory even had to smile at that. "Thanks for that back there. I think I was about to know what it felt like to fall asleep standing up."

"It's no problem, you looked a little trapped and my friends and I thought one of us should save you while the rest set up the sub-party."

"There are more of you? I thought I was practically the only person under the age of thirty in that room! Why did you rescue me? You don't even know me."

"Relax Rory. It's been a while but you haven't changed much in eight years. Apparently I have though-Ah! We made it!" He reached for the door handle and opened the door to laughter and loud music. "Look what I found boys!" Derek called out to the room.

She heard a collective "Rory's here!" from three or four people and the rest of the room echoed their cry.

Glancing to the left Rory felt a wave of panic as she noticed the door to her room was wide open and she was sure she'd left an assortment of clothing and underwear scattered across the floor and bed. She ran as fast as any Gilmore could and slammed the door shut with force, breathing out a sigh of relief. She turned around to find amused looks on the faces of a dozen or so guests.

"Don't worry Luv, we didn't see anything embarrassing," Finn assured her.

Logan held up his hand and Rory was distracted by the satisfied grin on his face, "Unless you would consider these embarrassing?" Looking away from his face she noticed that Logan was holding something on his finger.

_Pink butterfly panties? Why would that- "_Oh my God! You stole my underwear!" She darted toward Logan and quickly snatched her belonging back and jammed it into her purse. She pointed her finger at him and unleashed her rant, "This is a new low, even for you Huntzberger! I can't believe I actually thought you meant it when you said that you were done pranking. I guess the joke really is on me! You're the most vile, arrogant-"

"Whoa, hey, don't wave that finger at me and get all accusatory! It wasn't my idea! One of these idiots here decided they wanted a souvenir to show around school. I was merely saving you from a future as the Hartford Hussie." He looked pleased with his alliteration, walked over to her and put his hands on both of her shoulders. "Okay? Calm down, have some drinks with us and relax!"

"Hey bro, get your hands off my woman!" Derek joked and gave Logan a playful shove. "I just got her back and you're already trying to take her away from me."

Logan laughed and raised his hands in defense, "Hey sorry man, I just figured, since mom always taught us to share, that you wouldn't mind."

Rory looked from Derek to Logan and back to Derek again. _Mom? _"You're Derek Huntzberger? I can't believe I didn't recognize you! I had the biggest crush on you when we were kids and-"

"You had a crush on him? I thought I was your favorite Huntzberger. It's because he's older, right? Figures. Logan Huntzberger, Derek's little brother; that's all I am."

"Aw, I'm sorry little bro. I guess that extra eighteen months just makes all the difference with the ladies. Plus, I'm a college man." He patted Logan on the shoulder in comfort.

"What about me? I'm exotic!" Finn called out from behind them.

"So's the Asian bird flu!" Colin declared.

The room broke out into laughter, drinks were passed, and the night Rory had been dreading became one of the best in her life so far. Rory questioned Derek on life in college and learned that, of course, he attended Yale as a business and journalism major, preparing to take over the family business someday. She also learned that Logan too was Yale bound and immediately saddened at the realization that he would be attending college next year along with Finn and Colin (also going to Yale) and she would still be stuck in high school hell.

The other guests slowly faded out, but Logan, Derek, Finn, and Colin stayed behind talking about life and future plans. The four boys were going to take a boat trip over the summer to celebrate graduation. Being so close in age, Logan and Derek grew up best friends and Colin and Finn were more like brothers to them than friends. They also had a sister, Honor, and Rory vaguely remembered her. She was four years older than Derek so, being a teenager, she wasn't around much when Rory had spent time at the Huntzberger mansion one summer while Lorelai was working odd hours. As the conversation turned back to Rory, they were interrupted by a person fumbling with the door handle, trying to enter the pool house.

"Rory? I know you're in there! Come help mommy with the door. I can't work the knobby thing…" Rory rolled her eyes at her, obviously, drunken mother and glanced over at the clock, _12:30! _How had so much time passed? She was supposed to leave with her mom hours ago.

"Coming mom!" She quickly got up from the couch and ran over to the door to help her mom in.

Slightly tipsy and balancing a large bottle of champagne in her arms along with her purse and a champagne flute, Lorelai stumbled into the pool house and took in her surroundings, the smile dropping from her face. After dropping the contents of her arms onto the counter Lorelai turned to face the group in the sitting area, all of whom looked a little worried. "So, I leave you alone to go to the bathroom for five minutes and you disappear and have a party of your own? Way to leave me hanging kid. Dad wouldn't let me leave until I heard all of the Wiffenpoof's greatest tunes. I nearly started shoving salmon puffs in my ears!" The room visibly relaxed, but Lorelai was not pleased to find her daughter alone in a room with four young men. She instantly took a more sobering tone to voice her concern, "So, not that I don't enjoy a good get-together with friends, but I find it a little unsettling to find my teen-age daughter alone with four guys whom I've never met before."

Rory stood up to defend, "We were just talking mom! And you know two of them! Remember the Huntzberger's? This is Derek and Logan. Logan goes to Chilton and that's how I met these two, Colin and Finn." She turned to face the other four in the room, "Guys, this is my mom, Lorelai." She gave them a pleading look, trying to get them to be polite and acknowledge her mother as a figure of authority.

"Of course!" Derek spoke up first. "I'm Derek Huntzberger, this is my brother Logan. It's nice to see you again. It seems we've lost track of time, so the guys and I will leave you ladies to yourselves, come on guys."

As they headed for the exit, they all made plans to get together with Rory's other friends included. Lorelai helped to escort them out when Finn loudly spoke to Logan, "That's Rory's mom! My God that family's got good genes."

Rory giggled and looked up to her mother for her words of disappointment, but was met with another emotion altogether, "I like that Finn. Good choice in friends, kid. They can stop by any time, as long as they bring their flattery." Lorelai never said anything to Rory, but with one look, they came to an understanding that, at the very least, Lorelai would have to be aware that there were boys under her roof.

"I love you mom." Rory leaned in for a one-arm hug and walked to her room. She found herself smiling at the prospect of new friendships and then wondered how crazy and outgoing they could possibly be. These next few months were going to be a great adventure and she knew it.

**X**X**X**X**X**X**X**X*

_**That's it for this chapter! I am going to wrap up the Chilton phase of the story in the next chapter or two, but there is plenty more in store for these characters! I hope you all had fun reading! (And I hope my 4am delirium didn't ruin anything either!)**_


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